(2R,3r,4S)-3-(1-adamantyl)pentane-2,4-diol | 142205-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3r,4S)-3-(1-adamantyl)pentane-2,4-diol
• CAS: 142205-12-7；142236-59-7
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: DXBNBIRTBQMJGL-BCMPYHNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-(1-金刚烷)戊烷-2,4-二酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以60.6%的产率得到(2R,3r,4S)-3-(1-adamantyl)pentane-2,4-diol
  参考文献：
  名称：

  Diastereoselection in the LiA1H4 reduction of severely hindered β-diketones examples of -curtin-hammett preequilibrium conditions

  摘要：

  LiAlH4 Reduction of alpha-adamantyl (and tert-butyl)-beta-diketones occur under anti-Curtin-Hammett preequilibrium conditions, each preferred conformer leading to a different stereoisomeric diol, whereas reduction of 3-adamantyl-3-methyl (and ethyl)pentane-2,4-dione occurs with high diastereoselectivity to afford only the (2R, 3r, 4S) meso diol.

  DOI：

  10.1016/s0040-4020(01)88498-2

文献信息

• Diastereoselection in the LiA1H4 reduction of severely hindered β-diketones examples of -curtin-hammett preequilibrium conditions
  作者：Marcial Moreno-Mañas、Nicanor Galvez、Maria E. Lloris、Jorge Marquet、Antonio C. Siani

  DOI：10.1016/s0040-4020(01)88498-2

  日期：1992.1

  LiAlH4 Reduction of alpha-adamantyl (and tert-butyl)-beta-diketones occur under anti-Curtin-Hammett preequilibrium conditions, each preferred conformer leading to a different stereoisomeric diol, whereas reduction of 3-adamantyl-3-methyl (and ethyl)pentane-2,4-dione occurs with high diastereoselectivity to afford only the (2R, 3r, 4S) meso diol.